Ethyl Glycolate → HCID 86608509, compound

HRID 2113771Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11](=[O:22])[NH:12][C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:24]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1.CC#N.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:11](=[O:22])[N:12]([CH2:24][C:23]([O:27][CH2:28][CH3:29])=[O:26])[C:13](=[O:21])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione (0.34 mmol, 100 mg) in dry THF (1.0 mL) under an atmosphere of N2 at room temperature was added ethyl glycolate (0.34 mmol, 35 mg). The reaction mixture was cooled to 0° C. and tributylphosphine (0.17 mmol, 34 mg) was added followed by 1,1′-(azodicarbonyl)dipiperidine (0.36 mmol, 84 mg). After stirring at 0° C. for 10 min., the reaction mixture was brought to room temperature and the stirring was continued for 26 h. The reaction mixture was diluted with CH3CN:water 1:1 (2 mL) and purified using HPLC (95% 0.1M ammonium acetate buffer:5% CH3CN→100% CH3CN, 38.5 min., 25 mL/min.) to give 53 mg (41%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22-7.17 (bs, 1H), 7.15-7.05 (m, 3H), 7.01-6.96 (m, 2H), 6.63-6.52 (m, 4H), 4.36 (s, 2H), 4.24 (q, J=7.1 Hz, 2H), 3.69 (s, 3H), 1.30 (t, J=7.1 Hz, 3H).

Workup

customwas brought to room temperature
waitthe stirring was continued for 26 h
custompurified
customHPLC (95% 0.1M ammonium acetate buffer:5% CH3CN→100% CH3CN, 38.5 min., 25 mL/min.)

Sources & evidence

ORD record: ord-80672aeef71449b189dfaa2bc89b30aa
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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